Alex and Dave are dating again. Penny's accident leaves her in a full body cast, but when Max falls for her physical therapist, he tries to slow down her recovery. Brad hides a secret about his unemployed status from Jane.

Dave and Alex can't seem to agree on an apartment. When Penny needs a car, Jane negotiates for her. Max introduces Brad to the techniques for having a night out free.

Max has been working the Bar Mitzvah circuit as the professional "hype guy" - emceeing, getting the crowd excited and up and dancing. Penny convinces Brad to give it a try and partner up with Max, but when Brad turns out to be quite good, a little jealousy and tension begins to brew between the duo. Meanwhile, Jane encourages Dave and Alex to make a concerted effort not to take their relationship for granted this time around, but each of their separate attempts at romantic gestures seem to go right over the other's head.

Alex and Dave host Thanksgiving dinner at their new place, and Dave gets a little sidetracked by his desire to share his heritage with his friends and give them a real Navajo Thanksgiving. Meanwhile, Max gets his hands on a copy of the lost season of "The Real World" that he and Brad were on. The whole gang sits down and takes a walk down memory lane to when and how they all met 10 years ago - but also gain some added insight on things they weren't aware of.

Penny meets a terrific new guy, Pete, but her frantic attempt to hide the fact that she's wearing a prescription helmet because of her concussion really limits their potential romance; Jane, as always, tries too hard to break into the "boys' club" at the car dealership and enlists Brad to be her "trophy wife"; and Max and Dave's fist bump issues bring back painful childhood memories.

Jane and Alex's parents plan a huge party to celebrate the 20th anniversary of the family mattress business. Jane struggles for a joke to make her humorless dad laugh for her toast, while Alex quietly informs Dave that she hasn't told her mom and dad that they're back together. Max, feeling left out now that Penny's relationship with Pete is going so well, looks for a new BFF to replace her.

Nothing says the holidays like exposing a big lie! The gang is shocked to discover that Jane is really a Christmas baby and has been lying about her birthday this whole time because she hated being overshadowed by the holiday. So the group makes an extra special effort to throw her a Christmas-free birthday celebration - but will the holiday spirit prove to be too strong to fight?

When a hot young pop star stops in and buys a dress at Alex's store, Penny helps Alex turns it into a press opportunity... but not all publicity is necessarily good publicity. Meanwhile, Max is having an identity crisis, so Jane and Derrick take him on a tour of Chicago's themed gay bars to help him find his niche, and Brad and Dave try to be "men" and fix things around the house.

When a hot young pop star stops in and buys a dress at Alex's store, Penny helps Alex turns it into a press opportunity... but not all publicity is necessarily good publicity. Meanwhile, Max is having an identity crisis, so Jane and Derrick take him on a tour of Chicago's themed gay bars to help him find his niche, and Brad and Dave try to be "men" and fix things around the house.

Alex signs up the gang to participate in the Northside Kickball Classic tournament. However, self-appointed manager Max has difficulty bringing his players up to scratch - Dave has a history of freezing at crucial moments after an unfortunate incident during a previous game, Penny uses the tournament as an opportunity to meet good-looking guys and refuses to put on appropriate footwear, while Jane abandons her friends altogether and started playing for another team.

When Ryan, Jane's ex, comes to town for a visit, Brad is surprised to learn that Ryan is a woman. Meanwhile Max gets a super cool new roommate, Chase, who immediately upgrades the apartment with expensive furniture and gadgets. The gang is in awe, but when Chase suddenly disappears, they start snooping into his private life.

When the gang pranks Max into thinking he won a big lotto jackpot, he vows revenge when they least suspect it. Everyone dreads what might happen next; Alex decides to cut a deal with Max to avoid payback... while Max's plotting gets in the way of the big event Penny's been waiting for, a proposal from Pete. Meanwhile, Brad gets a new job as a CFO, but Jane is not amused when she learns the title is Chief Fun Officer and that Brad is working at a kids' gym.

When newly-engaged Penny learns that Pete wants to elope, would-be wedding coordinator Jane takes the lovebirds and the rest of the gang to a wedding expo in hopes that Pete will change his mind. Meanwhile, Max and Brad are stuck with a "couples" pass and end up in the gay wedding part of the expo, and Alex and Dave are forced to deal with their own unresolved wedding issues.

Brad uses his skills, plus help from the gang, to prop up Chuckles and Huggs after the gym's loopy owner, Terry, tells him it may be closing. Meanwhile, Penny and Max try to break the habit of texting the men in their lives (Pete/the new guy Max is dating). They turn to NocheTussin, a black market cough medicine, to help them sleep when they'd normally be texting.

Max meets a cute girl who is a season tickets holder for the Bulls, leaving him no choice but to pretend to be straight, of course! Meanwhile, Alex is tired of everyone dismissing her as the dimwitted blonde, so she becomes well read to prove them wrong. However her newfound knowledge completely throws the whole group dynamic off and no one likes it.

When Max tries out Jane and Alex's long-time hairdresser, Krisjahn, he gets some good salon gossip on the girls, but his loose lips may cause World War III between the Kerkovitch sisters. Meanwhile, the Steak Me Home truck is stolen and Dave and Penny try to figure out whodunit - but are perplexed by what they find when they finally locate the thief.

With the wedding coming up, Penny decides to reach out to her estranged dad Roy. The reunion is sufficiently awkward but Alex encourages Penny to be optimistic, while Jane is more skeptical. Meanwhile, Dave enlists Brad and Max's help in sabotaging "The Brazilian" food truck, a.k.a. Dave's #1 nemesis, but Max accidentally falls for the enemy's son and has to choose between his best friend or boyfriend.

Brad and Jane host a couples game night with Penny, Pete, Max and Scotty and the competitiveness gets a little out of hand, prompting Penny to make an unexpected move. Meanwhile Dave has a big decision to make on the career front, and Alex tries to help but they end up at a psychic instead

Penny insists that she's fine after her breakup with Pete, but the gang begin to wonder when she writes a play entitled 'Black Plague: A Love Story' and asks Derrick and his theater group to stage it. They brace for 'drama' in more ways than one. Meanwhile a marketing group asks Alex and Max to be tastemakers, but is it a scam?

The gang is shocked when Penny rebounds from her breakup with Pete by having a torrid affair with the last man on earth they'd pick for her - the Car Czar. To make matters worse, she's temporarily living with Brad and Jane, who end up acting like disapproving parents. Meanwhile the friends pressure Max to get a job so he'll stop sponging off them. He decides to enter the 'Mr. Gay Gay Chicago' pageant, with Alex and Dave as his coaches.

Chase, the ex-roommate whose life Max ruined, says he'd like to take revenge and do the same thing to Max, but Max's life is so pathetic it's 'un-sabotagable.' Max vows to prove him wrong and asks Jane to help him get his act together. Meanwhile, Alex asks the rest of the gang for help when Dave challenges her to finally use her stockpile of Groupons.

Penny's mom, Dana, and Dave's dad, Big Dave, are in town visiting, and these two lovebirds are not only going strong, they've decided to adopt a baby together, prompting Penny and Dave to react the only way they know how - irrationally. Meanwhile, Brad and Jane want some time just to themselves and decide to try to join an exclusive tennis club, but unfortunately Max is on the scent and they can't shake him...or Alex.

The third Kerkovich sister, Brooke, is the alpha sister of the group, and Jane has the daunting task of planning a wedding for her more perfect and exquisite older sibling. Meanwhile, Brad is having a tough time himself dealing with Brooke's equally more perfect African American fiance, Elliot (guest star James Lesure), and Alex and Dave have a big secret they're hiding.